Dimethylformamide → 1-(4-methoxybenzyl)-3-methyl-5-nitro-1H-indazole

HRID 1039092Notes

Reaction equation

HRID 1039092 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[NH:4][N:3]=1.CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=1>>[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][N:4]2[C:5]3[C:10](=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=3)[C:2]([CH3:1])=[N:3]2)=[CH:29][CH:28]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 178434304HCID 178434304, compound

Product 1

HCID 669271231-(4-methoxybenzyl)-3-methyl-5-nitro-1H-indazole

Conditions

Temperature
0 °C

Procedure

3-methyl-5-nitro-1H-indazole (1.0 g, 5.6 mmol) was dissolved in DMF (11.2 mmol) and cesium carbonate (2.0 g, 6.2 mmol) added. The slurry was cooled to 0° C. and p-methoxy benzyl chloride (0.97 g, 6.2 mmol) added to vigorously stirred slurry drop wise. The slurry was stirred at 0° C. for 1 hour, the cooling bath removed and the mixture stirred at RT for 3 h. The mixture was diluted with 4:1 water:saturated sodium bicarbonate (200 ml), extracted with EtOAc (3×50 ml), the organic fractions combined, washed with brine, dried over Na2SO4, filtered and the volatiles removed in vacuum. The product was purified by chromatography on SiO2 eluting with 30% acetone:hexanes to give the titled compound.

Workup

  1. customthe cooling bath removed
  2. stirringthe mixture stirred at RT for 3 h
  3. additionThe mixture was diluted with 4:1 water
  4. extractionsaturated sodium bicarbonate (200 ml), extracted with EtOAc (3×50 ml)
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe volatiles removed in vacuum
  9. customThe product was purified by chromatography on SiO2 eluting with 30% acetone

Sources & evidence

ORD record
ord-55500b7a74cd4e8ea655f859a15117d1
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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